Acetonitrile → 3-Bromo-4-{4-[4-(tert-butyldimethylsilanyloxy)butyl]imidazol-1-ylmethyl}benzonitrile

HRID 923290Notes

Reaction equation

[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[N:14]=[CH:15][N:16](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(#N)C.[Br:40][C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][C:48]=1[CH2:49]Br)[C:44]#[N:45]>C(OCC)(=O)C>[Br:40][C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][C:48]=1[CH2:49][N:16]1[CH:17]=[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[N:14]=[CH:15]1)[C:44]#[N:45]

Participants

Conditions

Temperature: 40 °C

Procedure

To 4-[4-(tert-butyldimethylsilanyloxy)butyl]-1-trityl-1H-imidazole (3.95 g, 7.95 mmol) is added acetonitrile (300 mL). To this solution is added 3-bromo-4-bromomethylbenzonitrile (2.14 g, 7.78 mmol). The solution is stirred at 40° C. for 18 h. The solvent is then removed in vacuo and methanol (300 ml) is added. The solution is heated to 55° C. and stirred for 1.5 h. Saturated sodium bicarbonate is then added and stirred for 10 min. The organic solvent is removed in vacuo, and the crude product extracted into ethyl acetate and washed with water. The organic solvent is removed in vacuo to give the crude product. Chromatography (silica gel, 1:0 to 1:1 to 0:1 hexanes:ethyl acetate) gives the pure product. MS (ESI) m/z 448, 450 (M+H).

Workup

customThe solvent is then removed in vacuo and methanol (300 ml)
additionis added
temperatureThe solution is heated to 55° C.
stirringstirred for 1.5 h
additionSaturated sodium bicarbonate is then added
stirringstirred for 10 min
customThe organic solvent is removed in vacuo
extractionthe crude product extracted into ethyl acetate
washwashed with water
customThe organic solvent is removed in vacuo
customto give the crude product

Sources & evidence

ORD record: ord-a2fd5ea587f640c69f46d08d75e0cd3c
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278969B2

Reaction notes

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